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Best of Chicago - The Grand Tour plus 360 Chicago

Get your bearings in the USA’s third largest city by combining a comprehensive tour of both the north and south sides of Chicago with a breathtaking (and rapid) trip up to the 94th floor Observatory of 360 Chicago, formerly the Hancock Tower.

Get ready to see a wide array of landmarks, museums and historical Chicago sites on this comprehensive tour which also includes an unforgettable trip to the 94th floor of the famous Hancock Tower for some breathtaking views.

The itinerary, which uses a luxury motorcoach to get around and includes an informative local guide providing insight and background information, takes in both the north and south sides of the Windy City while visiting a multitude of sights:

North Side highlights of the tour include:

  • Central Business District one of the worlds financial hubs and always bustling with activity
  • The Loop the historical centre of downtown Chicago
  • State Street designated the great street by none other than Frank Sinatra
  • Richard J. Daley Plaza home to an untitled 15ft steel sculpture by Pablo Picasso
  • Wacker Drive a multi-level street winding its way through the city that has appeared in Hollywood films such as The Blues Brothers, Batman Begins & Batman The Dark Knight
  • The Chicago River its direction of flow reversed by a 19th century civil engineering master feat
  • The Magnificent Mile home to fine restaurants, nightlife, excellent shopping and several of the tallest buildings in the world
  • Lincoln Park fronting onto Lake Michigan this is Chicagos largest public park
  • Wrigley Field home to the Chicago cubs baseball team (wont be visited on game days)

South Side highlights of the tour include:

  • Grant Park referred to as Chicagos front yard and scene of President elect Barrack Obamas victory speech on 4th November 2008
  • Soldier Field home to the Chicago Bears NFL team
  • Adler Planetarium & Astronomy Museum the oldest planetarium in existence today
  • Shedd Aquarium the most popular cultural attraction in Chicago and at one time was the worlds largest aquarium
  • Field Museum of Natural History famous for the scope and size of its collection, and home to the most complete and best-preserved
  • Tyrannosaurus Rex fossil discovered yet
  • Art Institute of Chicago one of the USAs premier fine art galleries, renowned for its collections of Impressionist and American art
  • Jackson Park hosted the historic World's Fair Columbian exhibition in 1893
  • Lake Point Towers architecturally stunning and also the worlds tallest apartment building
  • Orchestra Hall home to the Chicago Symphony Orchestra
  • Navy Pier 1km long pier on the shores of Lake Michigan

Please bear in mind that you will not get off the coach and enter all of the places listed below however the tour will help you decide which ones to explore more thoroughly and show you where they are located.

Hancock Tower AKA 360 Chicago

As well as taking in all the landmarks and historical sites of Chicago, this tour includes a ticket for you to vist 360 Chicago (formerly Hancock Tower's Observatory)... on the 94th floor!

Not only are the views from the Observatory spectacular, the lifts that take you there are the fastest in the world, travelling at 20.5 miles per hour they will take just 39 seconds to get you up there. On a clear day you will be able to see 80 miles and 4 different states – Illinois, Michigan, Wisconsin and Indiana.

Experience Includes

  • Comprehensive guided tour of Chicago
  • Discover highlights of the South Side and North Side – a perfect overview of the Windy City!
  • Enjoy a scenic drive along the Outer Drive
  • Visit Lincoln Park, the Adler Planetarium, Wrigley Field and more
  • Tickets to visit Hancock Tower (360 Chicago) observation deck
  • Transport by air-conditioned coach

Experience Excludes

  • Optional gratuities
  • Refreshments
  • Hotel pick ups - the tour starts at the Grayline Chicago Office at the northwest corner or Michigan Avenue and Monroe Street
  • Transportation to and from the Hancock Tower - 360 Chicago


Daily, year round.

Departure location

Grayline Chicago Office - details on your voucher

Start times

9.30am, 11.30am and 1.30pm April to September. 9.30am and 11.30 for the rest of the year


Around 4 hours.

Terms & Conditions

  • The precise itinerary is subject to change depending on local conditions and unforeseen events.